The latest installment in the Spider-Man cinematic universe, Spider-Man: Brand New Day, includes a notable Easter egg for long-time comic fans: the character of Captain Jean DeWolff. Portrayed by Liza Colón-Zayas, DeWolff appears as Peter Parker's contact within the NYPD, a role that connects her to a classic yet dark chapter in Spider-Man's printed adventures.

Jean DeWolff was first introduced in Marvel Team-Up #48 in 1976, created by Bill Mantlo and Sal Buscema. She served as a police captain and an unofficial liaison for Spider-Man, often depicted with a distinctive fondness for 1930s fashion and automobiles, driving a 1932 Ford. Despite her relatively limited appearances, DeWolff has maintained a peculiar staying power in the comics, frequently appearing in alternate universes and adaptations, including Spider-Man Noir, Spider-Gwen, The Amazing Spider-Man 2 video game, The Spectacular Spider-Man animated series, and Insomniac's Marvel's Spider-Man.

Her most significant comic book storyline is undoubtedly "The Death of Jean DeWolff," a four-part saga that ran from The Peter Parker, The Spectacular Spider-Man #107 to #111 in 1985. Written by Peter David with art by Rich Buckler, this arc marked a dramatic tonal shift for the series, moving from standard superhero fare to a gritty crime drama. The story begins with DeWolff's murder at the hands of the Sin-Eater, a shotgun-wielding serial killer. Spider-Man and Daredevil's pursuit of the Sin-Eater had profound consequences, most notably leading to the first time Peter Parker and Matt Murdock discovered each other's secret identities.

"The Death of Jean DeWolff" is considered an early example of the darker, noir-influenced storytelling that became more prominent in comics following Watchmen. The narrative positioned Spider-Man as a vengeful detective navigating an '80s New York on the brink of collapse, a portrayal that resonated with readers and influenced subsequent character development.

The ripple effects of this storyline extended beyond DeWolff's immediate fate. The hunt for the Sin-Eater inadvertently led to the downfall of journalist Eddie Brock, who was ruined after publishing a false story about the killer's identity. This professional ruin was a key factor in Brock's transformation into the iconic villain Venom, as later established in Amazing Spider-Man #300.

Despite her canonical death, Jean DeWolff has retained a lasting presence in the Marvel Universe, partly due to later creators who have kept her memory alive. There was even a brief attempt to resurrect her in the 2016 storyline Clone Conspiracy. Her legacy is also seen in characters like Yuri Watanabe, who was introduced as a friend and admirer of DeWolff's, eventually becoming a significant figure in Marvel's Spider-Man universe as the Wraith. The appearance of Jean DeWolff in Spider-Man: Brand New Day serves as a direct callback to this influential, albeit tragic, period in Spider-Man's comic history.